A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones

Aimin Song, Xiaobing Wang, Kit Lam

Research output: Contribution to journalArticle

142 Citations (Scopus)

Abstract

Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.

Original languageEnglish (US)
Pages (from-to)1755-1758
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number9
DOIs
StatePublished - Feb 24 2003

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Ketones
Aldehydes
Condensation
Carboxylic Acids
Ammonia
Ethanol
Meldrum's acid
coumarin-3-carboxylic acid
ketimine

Keywords

  • Coumarin-3-carboxylic acids
  • Knoevenagel condensation
  • Meldrum's acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones. / Song, Aimin; Wang, Xiaobing; Lam, Kit.

In: Tetrahedron Letters, Vol. 44, No. 9, 24.02.2003, p. 1755-1758.

Research output: Contribution to journalArticle

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